Urban outdoor water conservation and efficiency offer high potential for demand-side management, but irrigation, greenness, and climate interlinks must be better understood to design optimal policies. To identify paired transitions during drought, we matched parcel-level water use data from smart, dedicated irrigation meters with high-spatial resolution, multispectral aerial imagery. We examined changes across 72 non-residential parcels using potable or recycled water for large landscape irrigation over four biennial summers (2010, 2012, 2014, and 2016) that encompassed a historic drought in California. We found that despite little change in irrigation levels during the first few years of the drought, parcel greenness deteriorated. Between summers 2010 and 2014, average parcel greenness decreased −61% for potable water irrigators and −56% for recycled water irrigators, providing evidence that vegetation could not reach its vigor from wetter, cooler years as the drought intensified with abnormally high temperatures. Between summers 2014-2016 as drought severity lessened, irrigation rates decreased significantly in line with high drought saliency, but greenness rebounded ubiquitously, on average +110% for potable water irrigators and +62% for recycled water irrigators, demonstrating climate-driven vegetation recovery as evaporation and plant evapotranspiration rates decreased. Transitions were similar for customers with both potable and recycled water; vegetation changes were dominated by the overarching climatic regime. As irrigation cannot always overcome drought conditions, which will become more severe under climate change, to maintain vegetation health, utilities and urban planners should consider the tradeoffs between providing green spaces and water scarcity. This includes evaluating the roles of climate-appropriate landscaping and adaptive reallocation of potable and recycled water resources to enhance water security. By addressing emerging themes in urban water management through analysis of data from forthcoming water metering and aerial imagery technologies, this research provides a unique perspective on water use, greenness, and drought linkages.